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The reaction has been described in the literature [3] as proceeding in a manner similar to the Fischer indole synthesis. Here, the acid-catalyzed proton transfer first converts the cyclohexanone phenylhydrazone 1 to the intermediate 2. Subsequently, a heat-induced sigmatropic reaction occurs to produce 3, which is protonated and cyclizes into 4.
It reacts under acid catalysis with alcohols to 3-alkoxyenones. [2] Its pK a is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which also exists predominantly as the enol. [4]
Several routes exist for the production of cyclohexenone. For the laboratory scale, it can be produced from resorcinol via 1,3-cyclohexanedione. [6] Cyclohexenone is obtained by Birch reduction of anisole followed by acid hydrolysis. It can be obtained from cyclohexanone by α-bromination followed by treatment with base.
Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [11]. C 6 H 12 + O 2 → (CH 2) 5 CO + H 2 O. This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid.
1,4-Cyclohexanedione is an organic compound with the formula (CH 2) 4 (CO) 2. This white solid is one of the three isomeric cyclohexanediones . This particular diketone is used as a building block in the synthesis of more complex molecules.
The reaction conducted in two steps beginning with the conversion of DMT to the diester dimethyl 1,4-cyclohexanedicarboxylate (DMCD): C 6 H 4 (CO 2 CH 3) 2 + 3 H 2 → C 6 H 10 (CO 2 CH 3) 2. In the second step DMCD is further hydrogenated to CHDM: C 6 H 10 (CO 2 CH 3) 2 + 4 H 2 → C 6 H 10 (CH 2 OH) 2 + 2 CH 3 OH. A copper chromite catalyst ...
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400–450 °C over alumina doped with zinc oxide or cerium oxide. [4] Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide and nitromethane.
Conjugated carbonyls react with secondary amines to form 3-aminocarbonyls (3-ketoamines). For example, the conjugate addition of methylamine to cyclohexen-2-one gives the compound 3-(N-methylamino)-cyclohexanone. Conjugated carbonyls react with hydrogen cyanide to 1,4-keto-nitriles. See hydrocyanation of unsaturated carbonyls.